Yarn conditioning process



.atente Apr. Q 1946 YARN QONDITIONIN G PRGCESS Joseph B. Dickey andJames G. MeNally, Rochester, N. Y., assignors to Eastman Kodak Company,Rochester, N. Y., a corporation of New Jersey No Drawing. ApplicationDecember 17, 1938, Serial No. 246,515

'7 Claims.

This invention relates to the conditioning of textile yarns and moreparticularly to the condi- V tioning of filaments and yarns composed oforganic derivatives of cellulose such as cellulose acetate, cellulosepropionate, cellulose acetate propionate, and cellulose acetatebutyrate, to render them more amenable to textile operations such-asknitting and the like.

As is well known in the manufacture of yarns, particularly thosecomposed of or containing cellulose organic derivatives, it is necessaryto treat the yarn in order to reduce the tendency toward breakage of theindividual filaments or fibers when they are subjected to variousmechanical strains and to lubricate the yarn in order to facilitatehandling in such operations as spinning twisting, winding and reeling.It is also necessary to treat yarn to adapt it for-use as warp orfilling or for the manufacture of various types of knitted fabrics. Inknitting, it is particularly important that the yarn be soft and pliablein order that it may conform readily to the contour of the needles andthus produce a closely knit fab-- ric free from such defects as stitchdistortion, pin holes, laddering, and the like.

Heretofore it has been proposed to employ softening agents such aspolyhydric alcohols and similar agents as ingredients of yarnconditioning or lubricating formulas, generally in connection withmineral, animal or vegetable oils. It has been found, however, that mostof the known softening agents and the various formulas containing themhave certain drawbacks, one of the most serious of which is high vaporpressure, and in some cases too drastic a solvent action on the yarn.Many of such agents possess slight or insufiicient solvent power for thelubricants with which they are used, and it is accordingly necessary toemploy blending agents or emulsifying agents in order to obtain operableyarn treating formulas. In addition, many of the known softening andlubricating agents are insufl'iciently soluble in water to permitsatisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely newclass of yarn conditioning agents which are particularly adapted for thetreatment of yarns composed of or containing organic derivatives ofcellulose and capable of lubricating, softening and rendering such yarnsmore amenable to knitting and other textile .operations. A further andspecific object is to provide a class of conditioning agents whichaugment or assist the lubricating action of various lubricants whenapplied to such yarns. A still further object is to provide yarnsoftening and lubricating formulas which can be readily removed from theyarns by the usual scour baths.

A still further object is to provide an improved method for theconditioning of yarns, particularly those composed of or containingorganic derivatives of cellulose such as cellulose acetate,

whereby the yarn is rendered soft and pliable ing invention which, inits broader aspects, comprises the discovery that morpholine derivativehaving the general formula:

o-onR N(cH 0 CHg-CH: where a: and n are l, 2, 3, -etc., and R is asubstituent selected from the substituted and unsubstituted aromatic,hydroaromatic, aliphatic and heterocyclic groups, may be used as yarnconditioning agents and particularly as softening agents, with orwithout the addition of animal, mineral, or vegetable oils, in thetreatment of yarns composed of or containing organic deriva tives ofcellulose. We have found that these compounds when employed as describedin the detailed examples set forth below have a slight solvent and/orsoftening action on cellulose organic derivative yarns which renderssuch yarns soft and pliable without at the same time having too drastican action thereon.

These compounds may be prepared by treating hydroxyalkylated morpholinederivatives with the desired acid, acid chloride, or anhydride by knownmethods. In case an acid is used, the compound may be esterified byremoving water by means of an azeotropic withdrawing agent.

Examples of the preparation of typical compounds of this type are asfollows:

PREPARATION or Es'mns Morpholine ethyl furoate 143 parts of furoylchloride and a solution of 50 parts sodium hydroxide in 225 parts waterare added simultaneously to 130 parts morpholine ethanol, with vigorousstirring. The temperature is kept at 15-20 by means of an ice bath. Themixture is thenstirred two hours, allowing the temperature to rise tothat of the room. The resultant aqueous oil mix is then extracted twicewith benzene (200 and. 100 parts). The benzene is distilled off atatmospheric pressure and the residue fractionated in vacuo. Morpholineethyl furoate boils at 190-195/21 mm. It is soluble in water.

Morpholz'ne ethyl tetrahydrojuroate Morpholz'ne ethyl succinate 118parts succinic acid, 120 parts morpholine ethanol, 150 parts toluene,and 1 part p-toluene sulfonic acid are distilled in such a way that thetoluene is continuously separated from the water formed and returned tothe reaction. The heating is discontinued when 18 parts of water havebeen collected. The solution is then treated with a small amount ofsodium bicarbonate, filtered, and the toluene distilled off. The residueis then fractionated in vacuo. The ester boils at 250- 255/6 mm. It iswater soluble.

In accordance with the invention these compounds may be applied directlyto the yarn during or after spinning, or may be added to the spinningsolution itself. We have found that these compounds have exceptionalsolvent powers which enable them to dissolve mineral oils and blown andunblown, drying and semi-drying, vegetable and animal oils andaccordingly they may be, and preferably are, employed asingredients ofyarn conditioning or lubricating formulaes in conjunction with agentswhich function wholly or partially as lubricants.

In the following examples and description we have setforth several ofthe preferred embodiments of our invention, but they are included merelyfor purposes of illustration and not as a limitation thereof.

Our invention will be more readily understood by reference to thefollowing examples in which typical applications of the invention areset forth.

Example 1 The compound:

I CHr-GH: H:C-N

CHI-CHI 4 H-O-C OCi1 u m-o-c 0-0i1 u (N -Glycerol morpholine dioleate)Example 2 A conditioning liquid is made up as follows:

Parts o N -ClHr-OOOC11HSL so I (N-B-Hydroxy ethyl morphollne lam'ate)Olive oil and applied to textile materials such as silk, wool,

V cotton, viscose, cellulose acetate, etc. as described in Example 1. Ifthe yarn is intended primarily for knitting, the amount of conditioningliquid applied may vary from 4-25% by weight of the yarn and if forweaving, between 1-5%. Cellulose acetate filaments or fibers treated asdescribed are quite soft and pliable and give improved results invarious operations such as weaving, knitting, etc. Other examples ofsuitable lubricants which are used as illustrated in Examples 1 and 2follow.

Other examples of yarn conditioning composiyarns, particularly thosecomposed of or containing cellulose acetate, cellulose acetatepropionate, cellulose acetate butyrate, and similar cellulose organicacid esters in accordance with our invention and which render such yarnssoft and pliable and especially well adapted for various textileoperations, particularly knitting, are as follows:

Example 3 Parts /C rG 2 O\ N-CaHe-O C O--C4He 80 CHPCHQ (N -propanolmorpholine valerate) Blown olive oil... 20

Example 4 E /0 H-CH: 0\ N-C:H4OCOCH3 20 (I) HC H2 C H3 (N-fl-hydroxyethyl-3,5-dimethyl (morpholine acetate) Light mineral il Example 5 H2 H2H2 H2 CC\ /CC\ 0 /N-CiH4-00 C-(CH2)2C O-O-CaHr-N /0 Ha Ha H2 H3B-Hydroxyethyl morpholine succinate 20 Sperm oil 80 Example 6 Ha Ha C-C0\ N-C H -O-OC-(CliflrCO OH CC H5 H3 'y-Hydroxypropyl morpholine adipale50 Blown sperm oil- 50 Example 7 C2 4 0 \NC2H4O C1H4O o 00- 4o O 0(N-fl-Hydroxy-B-ethoxy morpholine benzoate) Blown sperm oil. 60

Example 8 /GaH4\ OE:'N\ /O i can 2 H0 Q 0-GH:

(N-Glycerol morpholine acetate stem-ate) Neate-ioot 60 Oleyl alcohol 20tions which may be applied to various types of arcane Example 9 /C2H4CHZ CH2 I 0 'N-C2H4OCOCH CH2 20 CzH (N-fl-hydroxyethyl morpholiuetetrahydrofuroate) Dimethoxyethyl adipate 20 Blown neat's-ioot oil 60Example 10 Wat r s0 CrHl CHr-O 0-0 C:H4N 0 10 C 2H4 (N-fi-hydroxyethylmorpholine acetate Water soluble cellulose ester Glycerol acetone.

and"

Example 11 (N- -hydroxyethyl morpholin ogate) is extruded through fineorifices into an evaporative atmosphere. The yarns thus produced arepliable and suitable for knitting, when prepared by being wound, ortwisted and wound.

Any of the above compositions, may be applied to the yarn intended foruse in circular knitting by means of a bath, wick, spray, roller, pad orany suitable means. The amount of conditioning liquid applied may varybetween 5-25% by weight of the yarn. Usually, however, the amount ofconditioning liquid applied is about 10-15% by weight of the yarn. Yarncomposed of cellulose acetate conditioned as described above givesexcellent results when used in the circular knitting process.

As will be apparent from the above examples and description theconditioning agents of our invention may be applied by a wide variety ofmethods. For example, we may employ the agent as an ingredient of thespinning dope from which the filaments are formed, the amount of theagent so employed depending upon a number of factors, such as theparticular cellulose derivative used in making the yarn, the solvent orsolvent combination used in making up the spinning solution, and thedegree of softness or pliability desired in the yarn, etc. Y

If the conditioning agent is to be applied to the yarn after spinning,this may be done by bringing the yarn in contact with a wick, roll, orfelt wet therewith, or the liquid may be applied by immersion, spray, orotherwise. The particular point at which the liquid is applied may vary.It may, for example, be applied to the yarn inside or outside thespinning cabinet, between the guide and godet roll, between the godet orother roll or guide and the point of winding and/or twisting. In somecases, the liquid may even be applied to the yarn after winding ontocones, spools, bobbins, or the like or by the so-called bobbin to bobbinmethod. In the case of staple fiber manufacture, the liquid may beapplied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon theresults desired, the specific nature of the material to which the agentis applied, the use to which the yarn is eventually to be put and otherfactors. For example, in a given case where a cellulose organic acidester yarn such as a yarn composed of cellulose acetate, is intended forknitting, about 4 to 25% or more by weight, based on the weight vents,emulsifying agents, blending agents and the like, may be added withinthe scope of our invention. Likewise, various dyes or other coloringmatter may be included in case it is desired to permanently orfugitively. tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention byreference to compositions containing specific percentages of the variousingredients, these percentages may vary widely depending upon theparticular purpose for which the composition is intended. For example,if it is desired to control the solvent or softening action of theconditioning agent, the amount of the agent may be adjusted as, forexample, by reducing the amount of the agent and correspondinglyincreasing the amount of oil or other ingredient. I

While we have described our invention with particular reference to thetreatment of yarns composed of organic derivatives of cellulose such ascellulose acetate, the conditioning agents and formulas described hereinare applicable to the conditioning of many other types of cellulosederivative yarns such as those composed of or containing cellulosepropionate, cellulose butyrate, cellulose acetate propionate, celluloseacetate butyrate, ethyl cellulose, methyl cellulose, benzyl celluloseand others, as well asto the conditioning of silk, wool, cotton, viscoseand other natural or artificial materials. v

The term yarn as used herein and in the claims is to be understood asincluding a single filament, a plurality of filaments associated intothe form of a thread, either of high or low twist,

.single or multiple threads associated or twisted together, compositethreads composed of a mixture of natural and artificial filaments or acomposite thread formed by twisting together individual strands ofnatural or artificial materials, as well as cut staple fibers producedfrom natural and/or artificial filaments or threads and spun yarnproduced from such staple fibers.

As indicated above, the yarn conditioning agents of our invention areexceptionally good solvents for a wide variety of mineral, blown andunblown, drying and semi-drying animal and vegetable oils such ascottonseed, olive, castor, neats-foot, sperm and other oils. Thisenables them to be used with any of such oils in making up a variety ofyarn treating formulas of varying composition.

The yarn conditioning method and compositions of our invention possessmany outstanding advantages. The fundamental and outstandingcharacteristic of the agents employed in accordance with the inventionis their ability to soften yarns, especially those composed of orcontaining organic derivatives of cellulose such as cellulose acetateand render them soft and pliable and amenableto various textileoperations, especially operations such as those involved in weaving andknitting where complicated designs or stitches are employed, without toodrastic an action onthe yarn material. Another outstandingcharacteristic of these compounds is their exceptional solvent power fora wide variety of mineral, animal, and vegetable oils and their abilityto act as lubricating assistants in conjunction with these oils whenapplied to such yarns. In addition, due to their solubility iri water,they may be readily removed from yarns and fabrics by means of the usualaqueous scour baths. By employing the yarn conditioning agents andmethod of our invention as herein described, one is enabled to obtainhighly satisfactory results in the manufacture of yarns and wovenfabrics and especially the production from these yarns of closely knitfabrics free from defects such as pin holes, stitch distortion,laddering and the like.

What we claim is:

1. The process of conditioning yarn to render it more amenable totextile operations including knitting, weaving, spinning and the likewhich comprises applying thereto a lubricating and softening compositioncontaining as its essential lubricating and softening component aN-hydroxy -alkyl morpholine ester.

2. The process of conditioning yarn composed of or containing organicderivatives of cellulose to render it more amenable to textileoperations including knitting, weaving, spinning and the like moreamenable to textile operations including knitting, weaving, spinning andthe like, which comprises applying thereto a lubricating and softeningcomposition containing as its essential lubricating and softeningcomponent a N-hydroxy alkyl morpholine ester.

4. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component a N-hydroxy alkylmorpholine ester and a textile lubricant.

5. Textile yarns amenable to textile operations including knitting,weaving, spinning and the like impregnated with a lubricant containingas its essential lubricating and softening component a N-hydroxy alkylmorpholine ester.

6. Textile yarns composed of or containing organic derivatives ofcellulose amenable to textile operations including knitting, weaving,spinning and the like, impregnated with a conditioning agent comprisinga N-hydroxy alkyl morpholine ester.

'7. Textile yarns composed of or containing organic derivatives ofcellulose amenable to textile operations including knitting, weaving,spinning, and the like, impregnated with a conditioning agent comprisinga-N-hydroxy alkyl morpholine ester and a textile lubricant.

JOSEPH B. DICKEY. JANIES G. MCNALLY.

